Halloween Dress-up

"Tim, can you please come on over? I have to go to a party later, and I'm already dressed in costume."

"Why are you dressed up so early?"

"I had to take my little brother Teddy trick or treating. But now my parents have taken him to a party at the club."

Even though I was a guy, and she obviously wasn't, Sally Brown was my best friend, and had been since we were kids. A few months before we had turned eighteen, Sally's dad had won the lottery. Sally's folks had moved into a fancy ranch house on a new golf course miles out of town. They had insisted that Sally finish high school in private school, so we had to really scramble to see each other. Usually, that meant Sally driving into the city to visit me, since she had been given a car last birthday.

Tonight, however, was Halloween and to my shock, Sally had plans. She was going to a party. Without me. I was surprised at how this made my stomach churn, my heart sink.

I gulped, regaining my composure. To buy time, I nervously asked, "How was trick or treating?"

"Well, some old perv showed me his thingy."

"Yuck, what did he do?"

"He just came to the door in a ratty old bathrobe. When Teddy turned to leave, I was still holding the door. The perv just brushed the robe open with his hand. His thingy was drooping out just like his sweaty tongue. I tried not to look, but then I met him in the eye and he grinned at me and wet his lips. I felt like Little Red Riding Hood meeting the Big Bad Wolf, and you weren't there to be my brave Woodsman."

"Is that what you dressed up as?"

Sally laughed a deep belly laugh. Though she had long hair and a curvy figure, she was never afraid to be just one of the guys. "Not anywhere close. The party is a themed event, one of the kids at my new school is hosting. His parents are away, so he dared us to be really wild."

At the mention of this classmate, I again felt tense. "So what are you?"

This time Sally's laugh was all girl, a series of rising soprano trills. "I'm not telling," she said, teasing. "You have to come over to see."

"So what did you do after the old man showed you his ...." I paused, unsure what word to use.

"His dink?" Sally suggested. "You'd think a perv would be all hard and stuff when he flashes. But this guy had a wrinkled little thing, and it was just dangling there."

"How do you know it was little?" The question was out of my mouth before I thought about it. For years, Sally and I had talked about everything. Puberty hadn't changed that. We talked girly stuff when she needed makeup tips and football when it was the season. Since her move, however, it all felt a bit weird.

"Because I've seen how lumpy your pants get when there's a sex scene in a movie, and felt how big it is when we took those dance classes before junior prom. I always wondered whether holding just any girl makes a boy that stiff. Or whether it was me especially doing it to you."

I was really glad at that moment we were talking on the phone, because if Sally had asked me that in person, my blush would have told her all she needed to know. I was speechless again, struggling with strange emotions. I wondered whether to risk my best friendship and tell Sally how I really felt. I did not dare tell her that I lay awake at night, my cock throbbing, until I learned that if I caressed the shaft just right, my balls would draw up tight to my groin. That I would picture her last summer, at her Dad's country club, climbing out of the pool, water droplets flying off her hair, her tanned skin glowing, her breasts bursting out of a teeny tiny bikini top. Thinking of that would always make my hand stroke faster. My fingers would be clenched around my rod, the tips of my nails grazing the tender flesh of my scrotum at one end and the lap beneath my head at the other. It seldom took long before the slit at the end of my helmet would start gasping like a dying man in a dessert, as I imagined her full plum lips kissing the tip of my tool. Sleep would follow only after the explosion of goo. I usually drifted off imagining Sally licking me clean.

Suddenly, in the silence, I wondered if my best friend swallowed. In fact, whether she was still a virgin. Surely, she would have told me if she lost it. But then, she hadn't mentioned this party. If I had not called, I would never have known about it. We never went to Halloween parties. Those were for cool kids, and we had never been part of that crowd.

"Who's this guy having the party?" I stammered, asking possibly the worst question to break the silence.

"Oh, Chad. He's kind of cool. You'd like him. Not a typical private school rat at all. Seriously strange."

I wanted to ask just how strange, and how she knew, but wasn't sure I was ready for the answer. Despite my confusion, I was certain of one thing. My trusty penis was threatening to burst our of my zipper, and the only solution was to see Sally face to face, if only to see what she was wearing which had inspired the old perv.

"But I don't have a car." I said. "How will I get out there?"

This time, Sally's laugh was plain wicked. I wondered at that instance if she was dressed up as a sexy witch, a bustier pushing her plump boobs towards her chin, nipples threatening to pop loose, knee high boots and a cape over a short tight leather skirt. Just the possibility almost made me come in my pants without even touching my aching organ.

"If you want to see me, I'm sure you'll find a way. But hurry. Chad said he locks the doors at midnight, so I haven't got all night."

The rush of confused emotions sent shivers through my spine. From there, it surged through my balls up my shaft. I had never felt so turned on, but so afraid. I was afraid that I was too excited by Sally as a female. I was afraid I would lose her as a friend. I was afraid she would lose it tonight with Chad, if she hadn't already. I was afraid that I would never get sex. I was afraid at trying sex with Sally, and disappointing her. I was mostly afraid that I would come in my pants before I got to her house.

"I'll be there within an hour," I promised.

I raced out of the house after hanging up the phone, glad that my Mom and Dad had already left for whichever bar they were frequenting these days. My alcoholic parents were a big reason why growing up an only child, I had wished that Sally was my sister. Now, it felt a bit like I was contemplating incest.

Instinctively, I ran over to the nearest busy intersection, and stuck out my thumb. Hitchhiking is a lost art, because of the risks, but Sally and I had frequently used that as a way to escape the confines of the trailer park, before she had escaped forever. I had never hitched alone before. As I stood in the chilly air, I realized that Halloween night might not be the smartest night to start. But I had promised Sally I would get to her house, and I sure didn't have cab fare.

A fancy convertible sports scar slid to a shuddering stop inches from my foot. Despite the season, the top was down. The driver was dressed as a ghost, white sheet flapping in the breeze. His date was dressed like a 1920s flapper girl. She was seated on the rear deck, her legs dangling over Casper's shoulders as she sipped straight from a mickey of gin. The nippy night, or the thrill ride had teased her nipples erect. They were threatening to pierce the flimsy fabric of her dress. As the driver spoke, I noticed that her lacy panties were clearly visible.

"Where you headed dude?" the ghost asked.

"West Grove Estates," I replied.

"Too bad I only give rides to strangers in costumes, then, cause I'm headed straight there." He laughed and roared off, his girl blowing me a mocking kiss as they vanished.

I stood shivering. There just wasn't much traffic on a Halloween evening. West Grove was at least a fifteen minute drive away. My promise to be there in an hour seemed impossible to fulfill. I slumped, dejected. Still confused about why I felt so strongly, I feared more than ever losing Sally, and had to admit, it was not her friendship which I feared losing. Just to make matters worse, it started to rain, a damp drizzle which matched my mood perfectly.

I started trudging along; thumb at half mast, wondering why I didn't just go home, when seemingly out of no where, a black SUV screeched to a halt, the plume of water from the tires miraculously missing me by inches. A motorized window hummed down, revealing that the vehicle contained a bevy of beauties. It was overcrowded so that counting instantly wasn't possible.

Someone said, "Hey , big boy, want a ride?"

I peered inside the vehicle. The driver was dressed as a naughty nurse, with red fright wig hair, overstuffed bra, almost nonexistent skirt, and white stockings with pretty lace tops. Next to her in the other bucket seat was the spokesman of the crew, a gum chewing harem girl, whose bra needed no Kleenex. Her well tanned cleavage was all real, and seemed to be threatening to jump out of the car and slap me in the face. In the back, I made out several girls literally piled on top of each other- a kitten, a ballerina, a chef, plus a few others buried beneath. A strong odour of booze wafted to my nose. Once again, the blood exited my brain and filled my cock.

"You look pretty crowded," I foolishly answered.

"Suit yourself," the driver growled, sounding miffed. When she pulled away, she seemed to take extra care to splash me with the plume of water off of her tires.

Dejected, I trod on along the road, the moonlight glistening off the puddles. At least the rain was slowing, but I could not stop thinking of what my beloved best pal Sally might be doing later with Chad. I pictured her as some total skank, an image of her I had never had before. I imagined that she would be scantily clad in a provocative costume. He would ply her with booze and then lead her to his bedroom. Despite the 'off limits' sign, another couple would be on the bed, except as Chad steered Sally to the mattress, Sally might notice that it was not just a couple but a threesome. She would be too drunk to care, but would still mumble "Chad, I can't."

"Why not, you're not a virgin, like that nerd Tim you hang with, are you? Maybe you prefer sissy boys?"

I pictured Sally shaking her head no, her long hair flying about her face, both Chad and one of the girls brushing it away from her face as she lay back. In my fantasy, my waking nightmare, Sally protested at the feminine touch. Chad would stroke her face, cooing reassuringly. "It's okay."

And then the girl would kiss her. "It's okay," the girl would repeat, her lips still brushing Sally's. The remaining couple would barely stir, but there might be a slight shift, so that they could watch this new thrill.

"It's okay," I heard Sally saying in my mind. As revolted as I was by these thoughts, I noticed that my cock stiffened despite the rain.

I stuck my thumb out again, though if no one serious stopped soon, I would give up. As I stood shivering, I pictured Chad taking Sally's arms and stretching them above her, while the strange woman distracted Sally, gently shifting her lips along Sally's throat, licking, then kissing, then licking more, finally, nibbling the soft porcelain skin. The other guy might move then to help Chad, producing a pair of handcuffs.

"It helps that you came as a cop," the final girl would slur, very drunkenly trying to suck the guy's cock, which had been limp until Sally had entered the room.

"He really must like these tits," she would respond, pulling Sally's top down, allowing her nipples to burst into the air.

This thought made me pause. I realized that I did not know what Sally's nipples looked like. Suddenly I resolved that best friend or not, and whether or not she was a virgin, my goal for this Halloween was to find out about Sally's nipples. In the meantime, my fantasy supplied generic light brown kisses, a tad bumpy in the chill.

I shook my head, trying to clear out the offensive yet exciting images. I wanted to scream 'No Sally,' like shouting out as another victim goes to their fate in a horror movie.

The two strange gals might shift their focus to the guy's rejuvenated erection, leaving Chad to slip along the bed and tweak Sally's nipples. He may reach over, though, and grab a hair clip from the first woman, releasing her flowing black mane as she licked her lover's meat. Chad would apply the clip to Sally's nipple, making her groan in pain, but then moan in pleasure. Suddenly, I sensed that the same perversity which initially repelled her might by then be exciting her.

Just as my mind tortured my soul with images of Sally voluntarily reaching over to free Chad's hardness from his costume, a monster truck skidded to a stop, drenching me with water. The passenger was a blonde girl, who looked barely eighteen, dressed as Raggedy Ann. I didn't have to see to guess that the driver would be her boyfriend, and he would be Raggedy Andy.

"Sorry about the water," the doll cooed, impossibly girlishly. "How can I make it up to you?"

An internal voice deep inside of me which I had never heard before wanted me to tell her that the only way she could even things up would be to strip herself, use her silly costume to dry me, and then suck my cock, swallowing my first load while her wimp boyfriend watched, and then letting me fuck her ass as he licked my cream pie from her cunt.

I was shocked. I never thought that way. I still did not say what I thought. Instead I replied, "I need a ride out to West Grove."

"No problem, hop in," Anne said, so I did.

It was cramped in the cab of the truck, so Anne, after a bit of uncomfortable squirming, her thighs rubbing against mine and Andy's on either side, hopped into my lap. My cock had deflated since the drenching, but the warmth of Anne's tush rubbing against my wet pants quickly revived my erection. I was afraid she might get upset that I was aroused. Instead, she sighed, and then it turned into a moan. She was clearly enjoying the ride.

I glanced over at Andy, but he was keeping his eyes on the road. I doubted that he could be unaware of what his girlfriend was doing. I figured he had to at least tolerate her pleasuring herself this way, or perhaps even be a bit excited by it. I knew that I was very thrilled.

Anne adjusted herself slightly. I felt the pressure from her pussy pushing down on my cock. The more Anne squirmed, the more fun we had. "What a waste of a good hard-on," she whispered, twisting around and pecking her lips on my ear.

"Oh, Andy, he's all hard," she said, then darted the tip of her tongue deep inside my ear. This in turn made my cock thrust harder at the fabric of my pants. Anne mewed like a kitten as she rubbed her bum along my zipper. She lifted her butt and resettled, so that she was higher in my lap. The tip of my rigid member would be piercing her pussy lips as she rocked back and forth if our clothes weren't in the way. All this while, Andy just drove.

After a few miles, he spoke," I bet she'd like it if you played with her titties. That really gets her off.

I hesitated, not really comfortable with the whole situation. Anne resolved my doubts though, grabbing my paws in hers and planting them on her bodice.

"Ouch," she exclaimed," not so hard. You aren't testing melons."

She again placed her hands over mine and spoke as she guided me. "Stroke them, and then squeeze softly. Start slowly. Yes, like that. Now spread your fingers wider and lift the weight of my flesh." She groaned loudly. "Now, now, now squeeze the nipple between your fingers."

She was still bouncing on my lap, riding my cloth covered cock.

"She can come just by having her tits played with," Andy explained. I had never heard of a girl doing that, but then, I was pretty inexperienced.

"My panties are getting all wet. If I stain this dress, the party shop will charge me extra," Anne pouted.

"Well, take the panties off, darling," Andy suggested.

Since the costume came with ankle socks, it was simple and easy for Anne to obey. She nonchalantly tossed the wispy cotton drawers over the rear view mirror, and then settled back on my lap, rubbing faster.

Without thinking, I began thrusting my hips up off the seat, matching her rhythm. She responded by pushing down harder.

"This is almost as good as fucking," Anne sighed, her words now separated by moaning. "Your pants are better for me than a condom. The roughness rubbing on my lips is a special thrill."

I thought I was about to blow my load in my pants. That never quite happened. Instead, Anne screamed, " I'm commmmmmminnnnng...." and collapsed back against me with final fierce wriggle followed by a triumphant giggle. Andy turned into the entrance of the gated community, coasting to a stop at a tiny guard house. Anne pulled herself together quickly, slipping back into the narrow middle space of the seat.

I could tell by the guard's posture that he was unimpressed by the monster truck. Fortunately, as he stepped closer, I saw it was one I knew from visiting Sally. He was an old retired cop, who liked supplementing his pension. I also knew that he liked night shift because the lighter traffic left lots of time for him to nip at his flask. Tonight, his nose was glowing so red that if it was Christmas rather than Halloween, he could be Rudolph.

"Oh, it's you, Tim. Here to see Sally?" He stared at Anne's tits, which were pushed up half out of the top, and had very apparent erect nipples.

"Even though I know you, not supposed to let you in with being on the list." He waved a clipboard. "Especially tonight, what with the residents worried about outside rowdies party crashing."

I was prepared for this familiar ritual. I reached into the pocket of my hoodie and pulled out a mickey bottle of rum. Reaching across, I passed it to the guard. With practiced speed, it vanished, hidden somewhere in his uniform.

"I suppose since you are a good friend of Sally, I can make an exception for you. Your friends can't take this heap of steel in though."

"That's fine", Andy replied, "We have our own party to go to anyway. We were just giving Tim a ride."

I started to open the door, but first, Anne grabbed my arm and pulled me close. Her tongue pressed between my lips. My mouth opened a bit in shock, so she inserted her pinkness in past my teeth, her tongue wrestling mine. Her left hand held the back of my neck as she continued swapping spit for what seemed like forever. Finally, she came up for air.

"See you soon, I hope," she breathed, exhaling slowly, slipping a note into my hand.

After I climbed gingerly to the ground, I saw that the note was her phone number. Andy turned around, and tooted his horn gently. He leaned out his window. "I'd love to watch you finish what she started," he said just as he drove off.

I was amazed by how this Halloween was unfolding, but for now I just shoved the note into a pocket and put the whole wild ride out of my mind. Sally was close by, and I felt ready to scale the Mount Everest of our attraction.

Sally's house was behind the third green, a short hike from the entrance to the club. Still, I was wet enough that the breeze off the pond used for irrigation chilled me to the core. The wisps of fog in the crisp fall air added a somber tone, bringing me down from the thrill of riding with Raggedy Anne and Andy. My member though was still rigid.

At least I was here almost exactly an hour after I spoke with Sally. That thought lifted my spirits as I lifted the ornate door knocker. I listened to the echo of the bong travel through Sally's father's tasteless tribute to newfound wealth. The developer could regulate the size and cost of the homes, but there was no governing good taste. The turrets and battlements were only appropriate once a year, and tonight happened to be the night. It looked every inch the Haunted House as I stood in the cold wondering whether I had missed Sally. Perhaps she had already gone to Chad's party, and my bad daydreams may be coming true.